(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol dihydrate hydrochloride

• ChemBase ID: 73049
• Molecular Formular: C20H29ClN2O4
• Molecular Mass: 396.90826
• Monoisotopic Mass: 396.1815851
• SMILES: c1cc2c(cc1OC)c(ccn2)[C@@H](O)[C@H]1N2CC[C@@H](C1)[C@H](C2)C=C.Cl.O.O
• Canonical SMILES: C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](c1ccnc2c1cc(OC)cc2)O.O.O.Cl
• InChI: InChI=1S/C20H24N2O2.ClH.2H2O/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;;;/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;1H;2*1H2/t13-,14?,19-,20+;;;/m0.../s1
• InChIKey: MPQKYZPYCSTMEI-WGGWNXAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol dihydrate hydrochloride
• IUPAC Traditional name: @quinine dihydrate hydrochloride; quinine dihydrate hydrochloride
• Synonyms: Quinine hydrochloride dihydrate; Quinine hydrochloride dihydrate; Quinine hydrochloride dihydrate; Quinine monohydrochloride dihydrate; Chinini hydrochloridum; 奎宁 盐酸盐 二水合物; Quinine 盐酸盐 二水合物; 奎宁 单盐酸盐 二水合物; 奎宁盐酸盐

Database IDs

• CAS Number: 6119-47-7; 6119-47-7
• EC Number: 205-001-1
• MDL Number: MFCD00151248
• Beilstein Number: 6112655
• PubChem SID: 162037969; 24848752; 24853558; 24853556
• PubChem CID: 16211283

CALCULATED PROPERTIES

• Acid pKa: 13.892048
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.7213722
• LogD (pH = 7.4): 0.863951
• Log P: 2.513464
• Molar Refractivity: 94.6936 cm^3
• Polarizability: 38.350784 Å^3
• Polar Surface Area: 45.59 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 115-116 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -144°, c = 1 in H2O; [α]20/D -230±5°, c = 2% in 0.1 M HCl
• Fluorescence: λex 322 nm; λem 450 nm in H2O; λex 347 nm; λem 448 nm in 0.5 M sulfuric acid

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥99.0% (NT); 90%
• Grade: Ph Eur
• Salt Data: dydrate+hydroch
• Suitability: suitable for fluorescence
• Impurities: ≤10% dihydroquinine hydrochloride (HPLC)
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C20H24N2O2 · HCl · 2H2O

DETAILS

Selleck Chemicals - S2502

Research Area: Infection
Biological Activity:
Quinine hydrochloride dihydrate is a natural white crystalline alkaloid having antipyretic (fever-reducing), antimalarial, analgesic (painkilling), anti-inflammatory properties and a bitter taste.It is a stereoisomer of quinidine which, unlike quinine, is an anti-arrhythmic. Quinine contains two major fused-ring systems: the aromatic quinoline and the bicyclic quinuclidine. It is very sensitive to ultraviolet light (UV) and will fluoresce in direct sunlight, due to its highly conjugated resonance structure. [1]

Sigma Aldrich - 145920

Other Notes
Remainder hydroquinine hydrochloride dihydrate
Packaging
10, 50 g in poly bottle

REFERENCES

• http://en.wikipedia.org/wiki/Quinine